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Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:47 UTC
HMDB IDHMDB0014917
Secondary Accession Numbers
  • HMDB14917
Metabolite Identification
Common NameNalidixic Acid
DescriptionNalidixic Acid is only found in individuals that have used or taken this drug. It is a synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum. It is an inhibitor of the A subunit of bacterial DNA gyrase. [PubChem]Evidence exists for Nalidixic acid that its active metabolite, hydroxynalidixic acid, binds strongly, but reversibly, to DNA, interfering with synthesis of RNA and, consequently, with protein synthesis.
Structure
Data?1582753235
Synonyms
ValueSource
1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acidChEBI
1-Aethyl-7-methyl-1,8-naphthyridin-4-on-3-karbonsaeureChEBI
1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acidChEBI
1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylic acidChEBI
1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acidChEBI
3-Carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-oneChEBI
Acide nalidixiqueChEBI
Acido nalidixicoChEBI
Acidum nalidixicumChEBI
NAKegg
NegGramKegg
1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylateGenerator
1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylateGenerator
1-Ethyl-7-methyl-1,4-dihydro-1,8-naphthyridin-4-one-3-carboxylateGenerator
1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylateGenerator
NalidixateGenerator
Acid, nalidixicHMDB
NevigramonHMDB
Sodium, nalidixateHMDB
Nalidixate sodiumHMDB
NalidixinHMDB
Sodium nalidixic acid, anhydrousHMDB
Anhydrous, nalidixate sodiumHMDB
Nalidixate sodium anhydrousHMDB
Sodium anhydrous, nalidixateHMDB
Sodium nalidixic acid, monohydrateHMDB
Chemical FormulaC12H12N2O3
Average Molecular Weight232.2353
Monoisotopic Molecular Weight232.08479226
IUPAC Name1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
Traditional Namenalidixic acid
CAS Registry Number389-08-2
SMILES
CCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C2
InChI Identifier
InChI=1S/C12H12N2O3/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14/h4-6H,3H2,1-2H3,(H,16,17)
InChI KeyMHWLWQUZZRMNGJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthyridine carboxylic acids and derivatives. Naphthyridine carboxylic acids and derivatives are compounds containing a naphthyridine moiety, where one of the ring atoms bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassNaphthyridines
Direct ParentNaphthyridine carboxylic acids and derivatives
Alternative Parents
Substituents
  • Naphthyridine carboxylic acid
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Methylpyridine
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point229.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.3 g/LNot Available
LogP2.1Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available145.251http://allccs.zhulab.cn/database/detail?ID=AllCCS00001033
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.3 g/LALOGPS
logP0.95ALOGPS
logP1.01ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)5.95ChemAxon
pKa (Strongest Basic)4.68ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area70.5 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity62.82 m³·mol⁻¹ChemAxon
Polarizability23.65 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.93831661259
DarkChem[M-H]-153.62831661259
DeepCCS[M+H]+154.00730932474
DeepCCS[M-H]-151.61130932474
DeepCCS[M-2H]-184.59330932474
DeepCCS[M+Na]+160.06130932474
AllCCS[M+H]+150.232859911
AllCCS[M+H-H2O]+146.132859911
AllCCS[M+NH4]+154.032859911
AllCCS[M+Na]+155.032859911
AllCCS[M-H]-153.832859911
AllCCS[M+Na-2H]-153.832859911
AllCCS[M+HCOO]-153.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Nalidixic AcidCCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C22704.4Standard polar33892256
Nalidixic AcidCCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C21856.2Standard non polar33892256
Nalidixic AcidCCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C22465.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Nalidixic Acid,1TMS,isomer #1CCN1C=C(C(=O)O[Si](C)(C)C)C(=O)C2=CC=C(C)N=C212223.6Semi standard non polar33892256
Nalidixic Acid,1TBDMS,isomer #1CCN1C=C(C(=O)O[Si](C)(C)C(C)(C)C)C(=O)C2=CC=C(C)N=C212451.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Nalidixic Acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fri-1790000000-92a3a10bfaccb41342fb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nalidixic Acid GC-MS (1 TMS) - 70eV, Positivesplash10-0079-8290000000-87bbcaf099e222302f022017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nalidixic Acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nalidixic Acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid LC-ESI-qTof , Positive-QTOFsplash10-014r-0590000000-0071689427e5460e95042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid LC-ESI-qTof , Positive-QTOFsplash10-053i-2920000000-a81650e261062799ba892017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid LC-ESI-QQ , positive-QTOFsplash10-001i-0090000000-b3f65ce918413bce9fa82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid LC-ESI-QQ , positive-QTOFsplash10-014i-0090000000-0ff01a82dbce74faefc62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid LC-ESI-QQ , positive-QTOFsplash10-014r-0790000000-46caea0fd853297971452017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid LC-ESI-QQ , positive-QTOFsplash10-000i-0900000000-3572ae3957b712815a4f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid LC-ESI-QQ , positive-QTOFsplash10-0zgr-0900000000-a89fdf787950fb2d88c22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid LC-ESI-IT , positive-QTOFsplash10-0a4i-0290000000-db7256d80ff333bc00bf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid , positive-QTOFsplash10-015i-0590000000-938c78d9d632c54cdffe2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid , positive-QTOFsplash10-014r-0590000000-0071689427e5460e95042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid , positive-QTOFsplash10-053i-2920000000-a81650e261062799ba892017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid 45V, Positive-QTOFsplash10-001i-0190000000-9f01c18c495b232328002021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid 60V, Positive-QTOFsplash10-0a4i-0490000000-2fbf36cc9f6f88d4cd652021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid 30V, Positive-QTOFsplash10-001i-0090000000-1d2b6985d9b92bbb98242021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid 15V, Positive-QTOFsplash10-001i-0090000000-3364d0d3d6ede5d5b1a42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid 75V, Positive-QTOFsplash10-0a4i-0950000000-f2b2776dbe2dc1e2e9be2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid 90V, Positive-QTOFsplash10-0pc0-0910000000-560515fc3b04b07a51e12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid 30V, Negative-QTOFsplash10-001r-3390000000-17e93f93f9a5f2cf26a12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nalidixic Acid 15V, Negative-QTOFsplash10-001i-1190000000-a192d15d35dfb6d306d72021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nalidixic Acid 10V, Positive-QTOFsplash10-001i-0190000000-fef5a9adccc5a0a5ec052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nalidixic Acid 20V, Positive-QTOFsplash10-00li-0890000000-c72282680d1ade35245c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nalidixic Acid 40V, Positive-QTOFsplash10-00ds-1900000000-4659dda7bb11b31ca0ef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nalidixic Acid 10V, Negative-QTOFsplash10-0019-0960000000-660f38f48e34b738382d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nalidixic Acid 20V, Negative-QTOFsplash10-0a4r-0900000000-76a76cfafed1c3238f422016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nalidixic Acid 40V, Negative-QTOFsplash10-0a4i-1900000000-1b71f0a68ff3448016e32016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00779 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00779 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00779
Phenol Explorer Compound IDNot Available
FooDB IDFDB020181
KNApSAcK IDNot Available
Chemspider ID4268
KEGG Compound IDC05079
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNalidixic_Acid
METLIN IDNot Available
PubChem Compound4421
PDB IDNot Available
ChEBI ID100147
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in tryptophan 2,3-dioxygenase activity
Specific function:
Incorporates oxygen into the indole moiety of tryptophan. Has a broad specificity towards tryptamine and derivatives including D- and L-tryptophan, 5-hydroxytryptophan and serotonin (By similarity).
Gene Name:
TDO2
Uniprot ID:
P48775
Molecular weight:
47871.215
References
  1. Sanzey B: Modulation of gene expression by drugs affecting deoxyribonucleic acid gyrase. J Bacteriol. 1979 Apr;138(1):40-7. [PubMed:108253 ]

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Sekine T, Watanabe N, Hosoyamada M, Kanai Y, Endou H: Expression cloning and characterization of a novel multispecific organic anion transporter. J Biol Chem. 1997 Jul 25;272(30):18526-9. [PubMed:9228014 ]